1. Field of the Invention
The present invention relates to a novel cyclopropanecarboxylate insecticide, to an insecticidal method and composition and to new intermediates in the preparation of this insecticide. More particularly, the invention relates to the preparation and insecticidal use of certain arylthiovinylcyclopropanecarboxylates.
2. Prior Art
Pyrethrins, naturally occurring extracts of chrysanthemum flowers, have long been of interest as insecticides. Since elucidation of the structures of these compounds, synthesis efforts have been directed toward preparation of related compounds having enhanced insecticidal activity and improved stability toward air and light. A noteworthy advance in this area was the discovery by Elliott, et al. of certain highly active compounds remarkably resistent to photo-oxidative degradation, for example, 3-phenoxybenzyl 3-(.beta.,.beta.-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate. This class of compounds is set forth in U.S. Pat. No. 4,024,163, issued May 17, 1977.
Since the discovery by Elliott, et al., there has been extensive research activity conducted in this area of insecticide chemistry. One such effort is disclosed in Belgian Pat. No. 851,465, published Aug. 16, 1977, which discloses certain phenylvinylcyclopropanecarboxylates as insecticides. In addition, U.S. Pat. Nos. 3,723,649 and 3,786,052 disclose certain other derivatives of vinyl cyclopropanecarboxylates and carboxylic acids.
In spite of the intensity of effort in this field, the phenylthiovinylcyclopropanecarboxylates have not been described prior to the present invention.
It has been found that these compounds are highly active insecticides, that they exhibit remarkable activity against insects of the order coleoptera and that they have excellent photo-stability.